A Removable Acyl Group Promoted the Intramolecular Dehydro-Diels–Alder Reaction of Styrene-Ynes: Highly Chemoselective Synthesis of Aryldihydronaphthalene Derivatives

Chen, Xia; Zhong, Cheng; Duan, Xianxian; Guan, Zhenhua; Gu, Lianghu; Luo, Zengwei; Chen, Yong; Zhang, Yonghui

doi:10.1021/acs.joc.2c00180

Cited by 6 publications

(5 citation statements)

References 49 publications

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“…Cyclopentane-fused naphthalenes were also successfully synthesized in up to 77% yield. 128 Intramolecular cyclization of acyl enynes 818 in the presence of 2,6-di-tert-butyl-4methylphenol (BHT) in 1,4-dioxane at 80 °C for 32 h gave aryldihydronaphthalenes 819 in good to excellent yields. The substrate scope included the halo group or electron-releasing groups The synthetic importance of the reaction was further demonstrated by performing the reaction on a gram scale, which resulted in the corresponding product in 82% yield.…”

Section: Review Synthesismentioning

confidence: 99%

Chemical Synthesis of Substituted Naphthalene Derivatives: A Review

Hussain,

Maheshwari

2023

Synthesis

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This review article outlines the progress made in the synthesis of substituted naphthalene derivatives. Naphthalene and its derivatives exhibit various biological activities such as anti-inflammatory, anticancer, antiviral, antitubercular, antimicrobial, antihypertensive, antidiabetic, etc. Several strategies have been developed in the past for the construction of naphthalene derivatives, primarily focused on Metal-catalyzed reactions (palladium, copper, zinc, rhodium, platinum, nickel, etc.,) and Lewis acid-catalyzed transformations. This review discusses the preparations of naphthalene derivatives using various salt such as gallium chlorides, gold chlorides, gold bromides, various gold complexes as well as bronsted acids like triflic acid and trifluoroacetic acid, and Lewis acids such as like boron trifluoride etherate. Additionally, miscellaneous reactions involving metal and Lewis acids are explored. The transformational approaches covered in this review include cycloadditions, carboannulations, benzoannulations, electroannulations, rearrangements, and cross-dehydrogenative coupling reactions. Overall this review provides a comprehensive and up-to-date account of the current state of preparations of substituted naphthalenes, highlighting their medicinal and industrial importance.

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Section: Review Synthesismentioning

confidence: 99%

Chemical Synthesis of Substituted Naphthalene Derivatives: A Review

Hussain,

Maheshwari

2023

Synthesis

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“…Several dearomative Diels–Alder methods have been reported in the literature to assemble functional , and bioactive molecules, , using either a thermal , or a catalytic approach. , In all cases, relatively harsh conditions (>150 °C) and/or strongly polarized substrates , are required. The product often has an aromatized naphthyl unit, and the isolation of the dihydronaphthalene derivative is rare (Scheme ).…”

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confidence: 99%

“…The sequence leading to 5 is the first example of a dearomative Diels–Alder cyclization using electronically unbiased partners. − ,− ,, Applications are at present limited to the use of extended aromatics, for which the intermediate dearomatization has a lower energetic cost compared to that of phenyl groups (such as those of enynes 1 ) because of the energy mismatch in the frontier orbitals involved in the cycloaddition.…”

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confidence: 99%

“…Polarized substrates are required in dearomative Diels–Alder cyclization. − ,− , We speculate that the donating ability of the carbonyl oxygen of the propiolate arm is crucial to ensure lithium coordination ( I ) , because no annulation occurred on ynones under identical conditions . The coordination polarizes the alkyne, paving the way for the dearomative Diels–Alder reaction.…”

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Sequential Strategies to Trigger Mild Dearomative Diels–Alder Cyclizations

et al. 2023

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Dihydronaphthalenes are present in several functional molecules, but their assembly is challenging. However, a sequential strategy can induce the key annullation of an alkyne with a vinylarene under mild conditions. Products form in good yields, with ample functional tolerance via domino nucleophilic substitution and dearomative Diels−Alder and ene reactions. DFT modeling data show that alkali cations are crucial to ensure a smooth dearomative cyclization on the in situ generated intermediates.

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“…The silver-catalyzed cyclopropanation of 1, n -enynes is relatively underdeveloped. Our ongoing interest in the propiolimide moiety has led us to investigate more intramolecular cyclization reactions of 1,6-enynes to afford valuable five-membered heterocycles . Herein, we demonstrate a highly efficient Ag(I)-catalyzed oxidative intramolecular cyclopropanation of nitrogen-tethered 1,6-enynes for the synthesis of 3-aza-bicyclo[3.1.0]hexane derivatives from imide materials under air conditions (Scheme e).…”

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confidence: 99%

Silver(I)-Catalyzed Oxidative Cyclopropanation of 1,6-Enynes: Synthesis of 3-Aza-bicyclo[3.1.0]hexane Derivatives

et al. 2022

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A simple Ag(I)-catalyzed oxidative cyclopropanation of heteroatom-tethered 1,6-enynes for the establishment of valuable functionalized 3-aza-bicyclo[3.1.0]hexane is presented, which allows the formation of multiple chemical bonds in one step under 20 mol % silver(I) catalysts and air conditions. This approach is highly atom economical, easy to perform, and free of external oxidants and features good to excellent yields and gram-scale synthesis. The preliminary study showed that an uncommon silver carbenoid intermediate might be involved in this process.

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A Removable Acyl Group Promoted the Intramolecular Dehydro-Diels–Alder Reaction of Styrene-Ynes: Highly Chemoselective Synthesis of Aryldihydronaphthalene Derivatives

Cited by 6 publications

References 49 publications

Chemical Synthesis of Substituted Naphthalene Derivatives: A Review

Chemical Synthesis of Substituted Naphthalene Derivatives: A Review

Sequential Strategies to Trigger Mild Dearomative Diels–Alder Cyclizations

Silver(I)-Catalyzed Oxidative Cyclopropanation of 1,6-Enynes: Synthesis of 3-Aza-bicyclo[3.1.0]hexane Derivatives

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